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通过 3-氧代吲哚的氧杂-1,3-偶极环加成反应,实现了最小溶剂化、无色谱分离、非对映选择性合成恶唑烷-二螺[吲哚啉-3,3'-吡咯烷]。

Solvent-Minimized, Chromatography-Free, Diastereoselective Synthesis of Oxazolidine-Dispirooxindoles via oxa-1,3-Dipolar Cycloaddition of 3-Oxindole.

机构信息

College of Chemistry and Chemical Engineering, Central South University , Changsha 410083, P. R. China.

College of Chemistry and Materials Science, Guangxi Teachers Education University , Nanning 530001, Guangxi, P. R. China.

出版信息

J Org Chem. 2018 Mar 2;83(5):2948-2953. doi: 10.1021/acs.joc.7b02865. Epub 2018 Feb 15.

DOI:10.1021/acs.joc.7b02865
PMID:29405065
Abstract

An efficient and diastereoselective decarboxylative oxa-1,3-dipolar cycloaddition between 3-oxindoles and diverse amino acids is developed to access novel oxazolidine-dispirooxindole skeletons bearing vicinal quaternary carbon centers. This protocol features operational simplicity, a broad substrate scope, and good to excellent chemical yields and diastereoselectivities. In particular, minimal solvent (1 mL/10 mmol) and chromatography-free purification render this synthetic process more efficient and environmentally benign in the context of green chemistry.

摘要

发展了一种高效的、非对映选择性的 3-氧吲哚与各种氨基酸的脱羧基氧杂-1,3-偶极环加成反应,以获得新型含有毗邻季碳中心的恶唑烷二螺[吲哚啉-3,3'-氧吲哚]骨架。该方法具有操作简单、底物适用范围广、产率和非对映选择性好等优点。特别是,在绿色化学的背景下,这种合成方法使用的溶剂最少(1 mL/10 mmol),且无需进行色谱纯化,因此更加高效、环境友好。

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